CN104053732A - Printing ink or overprint varnish with renewable binder component - Google Patents
Printing ink or overprint varnish with renewable binder component Download PDFInfo
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- CN104053732A CN104053732A CN201280067411.1A CN201280067411A CN104053732A CN 104053732 A CN104053732 A CN 104053732A CN 201280067411 A CN201280067411 A CN 201280067411A CN 104053732 A CN104053732 A CN 104053732A
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- ink
- lignin
- nitration
- xylogen
- printing
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/08—Printing inks based on natural resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D197/00—Coating compositions based on lignin-containing materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D197/00—Coating compositions based on lignin-containing materials
- C09D197/005—Lignin
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Printing Methods (AREA)
Abstract
The present invention is related to a printing ink, in particular flexographic printing ink, or an overprint varnish, comprising a nitrated lignin as at least one binder component, to a process for preparing the same as well as to the use of a nitrated lignin as a binder component in a printing ink, in particular a flexographic printing ink, or an overprint varnish.
Description
The present invention relates to printing-ink and overprint varnish zhe, relate to especially flexographic ink or gravure ink, it comprises nitration of lignin as at least one binder ingredients.
Gravure and flexographic printing are the main printing processes for printed apcksging material.These methods can be for printing various base materials, for example, and paper, fiber board or plastic basis material.Gravure and flexographic printing method are known.For example, can be with reference to Leach/Pierce (Eds.), The printing ink manu al, Blueprint, London, 5
thed.1993, p, 33-53.The characteristic of gravure ink and flexographic ink is also known for technician.For example, can be with reference to Leach/Pierce (Eds.), The printing ink manual, Blueprint, London, 5
thed.1993, p, 473-598.By reference by those chapters and sections separately in fit into herein.
A kind of main binder ingredients for gravure and flexographic ink is nitrocotton.Yet nitrocotton is more expensive in recent years, makes its use in printing-ink have economically less magnetism.Although the several synthetic binder ingredients for gravure and flexographic ink is known, due to environment, using recyclable materials is desirable as binder ingredients at least partly.Due to for such as sealing, pasteurization or sterilisation purpose, wrapping material are being manufactured by the thermal treatment of normal experience, and such bonding agent material also will must show that good thermal resistance is to be suitable as the component in gravure and flexographic ink.
Xylogen is the biological polymer appearing in timber.It is comprised of the phenol macromole (phenolic macromolecule) with different structure.Industrial, it is that by product as paper technology makes.By known kraft process (sulphate process) and/or sulphite process, can obtain alkaline xylogen or sulfonated lignin.These methods and the lignin product being made by it are being known in the art, and here there is no need to discuss in detail.
In nearest 20 years, such component in having applied as some from the alkaline xylogen of kraft process, comprises as rubber stock, by using xylogen to replace the wood composites of part resol or tackifier and the antioxidant of degradable thermoplastic polymer mixture in phenol-formaldehyde resin formula.Lignin derivative such as sulfomethylation xylogen has been used in the concrete composition that reduces concrete mixture water-content.Xylogen-phenol derivatives is for molded resin combination.In WO02/18504A2, the sulfonation and/or the sulfomethylation xylogen that at the water soluble dyestuffs preparation for ink jet printing, as dispersion agent, use have been described.
There is the disclosure of using as binder ingredients in printing-ink about the xylogen from above-mentioned kraft process or sulphite process.With reference to from the following patent of Westvaco company: US-5,192,361, US-5,188,665, US-4,957,557, US-4,891,070, US-6,045,606, US-4,892,587, US-4,612,051.Yet, it must be noted that, these old patents are commercially available to comprise xylogen as the printing-ink of binder ingredients from prematurity.Obviously, those formulas do not demonstrate it becomes the abundant character of nitrocellulosic substitute as the binder ingredients in gravure and flexographic ink.
Problem of the present invention is to provide printing-ink, particularly gravure ink or flexographic ink, and overprint varnish zhe, and it comprises binder ingredients, and described binder ingredients forms by having enough stable on heating recyclable materials at least in part.
According to the present invention, above problem is unexpectedly by printing-ink, and particularly gravure ink or flexographic ink solve, and it comprises the nitration of lignin as at least one binder ingredients.
According to the present invention, above problem is also solved by overprint varnish zhe, and it comprises the nitration of lignin as at least one binder ingredients.
According to the present invention, term " nitration of lignin " defines the nitrated product making by xylogen.
Especially, nitration of lignin according to the present invention is made by alkaline xylogen, and described alkaline xylogen is the product of kraft process described above.Substantially, in kraft process, use mineral acid to process the biomaterial containing xylogen, and do not apply heat.
According to the present invention, particularly preferably be and use according to being described in alkaline xylogen prepared by the method in WO2007/12440A2 (Greenvalue S.A.).To in WO2007/12440A2, fit into herein by reference.Substantially, xylogen from all kraft processes described above stands the processing of chemistry-thermomechanical, this chemistry-thermomechanical is processed under the additive existence being included in such as ethylene glycol, mechanical shearing under the top temperature of about 100-220 ℃ and under approximately 0.5 to approximately 10 atmospheric pressure, described additive reduces the softening temperature of described xylogen.Alkaline xylogen like this can be used as the dried powder of the commodity Protobind by name of ALM India sale and buys from the market.
The exemplary xylogen that is applicable to prepare nitration of lignin of the present invention is with commercial name Protobind2000 sale.It is essentially no sulphur (being less than 10%), has the softening temperature of approximately 130 ℃, has the number-average molecular weight of about 1000g/mol, and have 7 or the water-bearing media of less pH in be insoluble.Yet it is highly soluble in the water-bearing media having higher than 7 pH.For the conventional xylogen of common indissoluble, this is significant difference.Protobind series commodity water-soluble different.
According to the present invention, nitration of lignin is preferably by being described in GB-866, and 968 nitrifying method makes: by xylogen be suspended in the immiscible organic liquid of water in, described organic liquid is inertia to nitric acid, for example tetracol phenixin (CCl
4), dithiocarbonic anhydride (CS
2) or methylene dichloride (CH
2cl
2), and be no more than at the temperature of 28 ℃ and nitric acid (HNO subsequently
3) reaction, to avoid oxygenolysis.Inexcessive use nitric acid.By reference by GB-866, fit in 968 herein.
It should be noted in the discussion above that and the invention is not restricted to the nitration of lignin that made by above method.Also can apply other method of preparing nitration of lignin.For example, also can in organic solvent, under cooling and stirring, use the vitriol oil (H
2sO
4) and the mixture of concentrated nitric acid carry out nitrated.According to the present invention, for any method of nitration of lignin, be all suitable, described method can not cause not oxidative degradation and the method for expected degree to produce soluble nitration of lignin.
Nitration of lignin is soluble in the multi-solvents such as acetone, methylethylketone, ethanol or Virahol.According to the preferred embodiments of the invention, have been found that if nitration of lignin is not the mode of isolating to be stored, but be stored in 50% acetone soln, can keep favourable solvability feature.
The degree of nitrification of nitration of lignin of the present invention and their molecular weight can change.
For various application, preferably nitration of lignin component is used together with other tackiness agent.Have been found that nitration of lignin of the present invention demonstrates the abundant or good consistency with multiple urethane resin, ketone resin or polyamide resin.Therefore, nitration of lignin of the present invention can advantageously be used in combination.The example of compatible resin is the applicant's urethane resin, for example, is described in EP-1 229 090Al, EP-1 357 141Al, EP-1 361 236Al, EP-1 493 762Al, EP-1 496 072Al or EP-1 496 071Al.
Nitration of lignin component depends on the ink property that will obtain with the ratio of other binder ingredients that will use, and can easily be determined accordingly by technician.Described ratio can be subject to the restriction of the consistency of nitration of lignin component and other binder ingredients.
Nitration of lignin can be used as pigment tackiness agent in printing-ink of the present invention, especially for green pigment, or alternatively in the varnish such as overprint varnish zhe, is used as tackiness agent.
According to ink of the present invention, be as colored ink layer or varnish, can exist toner.According to the present invention, described tinting material is preferably pigment.According to the present invention, can use any pigment conventionally using in flexographic ink, for example, monoazo yellow (for example, CI Pigment Yellow 73 3,5,98), diarylide yellow (for example, CI pigment Yellow 12,13,14), gorgeous beauty (Irgalite) blue, forever admittedly your ruby red 4B, ruby red 2B, Lake red C, lithol red, permanent bordeaux R of orange G (Pyrazolone Orange), permanent bordeaux 2G, lithol, PHTHALOCYANINE GREEN 7 is green, PHTHALOCYANINE GREEN 7 is blue, permanent violet, titanium dioxide, carbon black etc.
Weight based on ink composite, the amount of normally used pigment is 5 to 60 % by weight, is preferably 10 to 60 % by weight.
According to the present invention, the amount that gives the independent component of printing-ink or overprint varnish zhe is understood, and makes the combination of all components amount to 100 % by weight.
By any conventional method, pigment is combined with adhesive material.According to the present invention, with the form being scattered in nitration of lignin, provide pigment.The dispersion of pigment in nitration of lignin can be passed through, for example, by polishing, undertaken.Example is ball mill, sand mill, horizontal medium grinding machine, the mobile grinding machine (high-shear fluid flow mill) of high-shear fluid etc.Typical pigments dispersion according to the present invention comprises the solution of nitration of lignin in the solvent such as ethanol, ethyl acetate, n-propyl acetate or their mixture, with pigment and optionally extra solvent (its can with solvent phase for nitration of lignin solution with) combine.
Weight based on ink composite, printing-ink overprint varnish zhe according to the present invention comprises 10 to 80 % by weight conventionally, is preferably the adhesive material of 40 to 80 % by weight.This can be a kind of combination in nitration of lignin itself or nitration of lignin and above-mentioned other tackiness agent.
Optionally, according to putting on the specific requirement on printing-ink or overprint varnish zhe, can add solvent and such as the additive of filler, tensio-active agent, varnish, wax, adhesion promotor etc.
According to the preferred embodiments of the invention, the weight based on ink composite, one or more additives that printing-ink or overprint varnish zhe comprise 1 to 10 % by weight.
As the additional solvent component that forms the surplus of printing-ink or overprint varnish zhe, can use such as the alcohol of ethanol, n-propyl alcohol or oxyethyl group propyl alcohol or such as the ester of vinyl acetic monomer or n-propyl acetate.
Printing-ink of the present invention or overprint varnish zhe can be as conventional flexographic ink or overprint varnish zhes, respectively by under suitable condition independent component mutually being mixed and made.
As mentioned above, according to the preferred embodiments of the invention, nitration of lignin component is provided as 50% acetone soln, thereby keeps good solubility.Therefore, the invention still further relates to the method for preparing printing-ink or overprint varnish zhe, particularly gravure printing ink or flexographic ink, the method comprises the following steps:
By nitrated alkaline xylogen, prepare nitration of lignin and described nitration of lignin is dissolved in acetone to obtain 50% acetone soln;
By the acetone soln of nitration of lignin be selected from tinting material (being preferably pigment), at least one solvent and optional additive in one or more components mix.
As described above, alkalescence xylogen nitrated preferably by being described in GB-866, nitrifying method in 968 is implemented: by xylogen be suspended in the immiscible organic liquid of water in, described organic liquid is inertia to nitric acid, for example tetracol phenixin, dithiocarbonic anhydride or methylene dichloride, and be no more than at the temperature of 28 ℃ and nitric acid (HNO subsequently
3) reaction, to avoid oxidative degradation.Inexcessive use nitric acid.According to the present invention, preferably, use CCl
4as solvent.Described reaction preferably carry out 2 to hour, be most preferably 4 to 8 hours.
According to the preferred embodiments of the invention, make water and use CCl
4the nitration of lignin that washing obtains thus.Have been found that by using those different solvent wash products, can from nitration of lignin, remove more impurity.
As described above, the product that the alkaline xylogen preferably using is in the method for the invention kraft process described above.According to the present invention, particularly preferably be, use according to being described in alkaline xylogen prepared by the method in WO2007/12440A2 (Greenvalue S.A.).To in WO2007/12440A2, fit into herein by reference.Alkaline xylogen like this can be used as the dried powder of the commodity Protobind by name of ALM India sale and buys from the market.The exemplary xylogen that is applicable to prepare nitration of lignin of the present invention is sold with business's name Protobind2000.With reference to detailed description above.
According to the present invention, have been surprisingly found that, nitration of lignin described above can be as the tackiness agent in printing-ink or overprint varnish zhe, particularly gravure printing ink or flexographic ink.As described above, nitration of lignin can be unique binder ingredients or can use with other resin-bonded compatible with nitration of lignin.
According to the present invention, have been found that some conventional tackiness agents that use in nitration of lignin and flexographic ink are compatible, this routine tackiness agent is for example multiple urethane resin, ketone resin or polyamide resin.
Very unexpectedly, compare with conventional ink or overprint varnish zhe based on soluble cotton adhesive material, printing-ink of the present invention and overprint varnish zhe demonstrate improved thermotolerance.Therefore, printing-ink of the present invention or overprint varnish zhe have the following advantages with respect to the ink based on conventional soluble cotton tackiness agent or overprint varnish zhe:
-because nitration of lignin can be obtained by alkaline xylogen cheap and that be easy to get, so they are more cheap;
-they are more heat-resisting, and they are for example more suitable for, for being subject to the application of heat treated print product (sterilization).
Now will use infinite example further to explain the present invention.
embodiment 1: nitration of lignin synthetic
According to being described in GB-866, the method in 968 example is prepared nitration of lignin.50 grams of xylogen are scattered in to the tetracol phenixin (CCl of 250ml
4) in.Use water cooling dispersion liquid, simultaneously under continuously stirring by 40ml concentrated nitric acid and 125ml CCl
4mixture divide carefully and add in a small amount double-deck reaction vessel.For fear of any oxidative degradation, allowable temperature does not rise over 28 ℃.After 6 hours, product is filtered, and make to wash with water, then use CCl
4washing, thereby except disacidify and impurity, and vacuum-drying.It should be noted that, at GB-866, in 968 example, reaction has only been carried out 2 hours.In order to ensure completely nitrated, extended the reaction times.Similarly, at GB-866, in 968 example, only use CCl
4washing reaction product.Find that this is not enough to obtain straight product.Therefore, comprised the additional step that makes to wash with water product.Make to wash with water in process, some part of observing product is soluble in water.
Find that nitration of lignin is soluble and in alcohol, is partly soluble in acetone.Yet, solid nitration of lignin was kept after a couple of days, acetone solution has reduced.So, in order to keep the solvability of nitration of lignin constant, prepared 50% acetone soln of nitration of lignin.Following ink embodiment has all been used this solution.
embodiment 2: the overprint varnish zhe with nitration of lignin
The following method of usining is prepared overprint varnish zhe: by mixing with the n-propyl acetate of the ethanol of 24.4 % by weight, the vinyl acetic monomer of 6 % by weight and 15 % by weight according to the nitration of lignin of embodiment 1 (acetone soln as 50%) of 54.6 % by weight.By the urethane resin (Surkopak5244) of the gained nitrolignin matter solution of 77 % by weight and 7.7 % by weight, the ethanol of 4.6 % by weight, the adhesion promotor of the wax of the oxyethyl group propyl alcohol of 7.8 % by weight, 1.4 % by weight (from the Luwax AF-31 of BASF, micronized polyethylene wax) and 1 % by weight (from the Vertec PI-2 of Johnson Mathey; This is titanate coupling agent (oxyethyl group titanium isopropoxide two (2,4-pentanedionate)).
comparative example 1: there is nitrocellulosic overprint varnish zhe
In order to compare, with the method for describing in embodiment 2, prepare overprint varnish zhe, difference is not use the nitrolignin matter solution of 77.5 % by weight, but the solution of the n-propyl acetate composition of the soluble cotton by 39 % by weight (SS1/8, IPA infiltrates (damped)) of use 77.5 % by weight, the ethanol of 40 % by weight, the vinyl acetic monomer of 6 % by weight and 15 % by weight.
embodiment 3: thermotolerance test
Use aluminium foil as base material.On described base material, apply conventional ink formulations (from the Access-Foil of Siegwerk).
On conventional ink layer, alternatively print from the overprint varnish zhe of embodiment 2 with from the overprint varnish zhe of comparative example 1.Thermal treatment products obtained therefrom.The product that discovery comprises from the overprint varnish zhe of comparative example 1 is stable up to 200 ℃.Yet the product that discovery comprises from the overprint varnish zhe of embodiment 2 is stable up to 250 ℃.Therefore, the overprint varnish zhe based on nitration of lignin is than more heat-resisting as the conventional overprint varnish zhe of main binder component based on soluble cotton.
Claims (15)
1. printing-ink, particularly gravure printing ink or flexographic ink, this ink comprises nitration of lignin as at least one binder ingredients.
2. printing-ink according to claim 1, wherein, described nitration of lignin can be by being no more than at the temperature of 28 ℃ and solvent obtains with the alkaline xylogen of nitric acid nitrating under existing, and described solvent and water are immiscible and are inertia to nitric acid.
3. printing-ink according to claim 2, wherein, described alkaline xylogen can obtain by making xylogen stand the processing of chemistry-thermomechanical, described chemistry-thermomechanical is processed under the additive existence being included in such as ethylene glycol, mechanical shearing under the top temperature of about 100-220 ℃ and under approximately 0.5 to approximately 10 atmospheric pressure, described additive reduces the softening temperature of described xylogen.
4. according to the printing-ink described in any one in claims 1 to 3, wherein, described ink comprises at least one extra tackiness agent, and described extra tackiness agent is selected from urethane resin, ketone resin or polyamide resin.
5. according to the printing-ink described in any one in claim 1 to 4, wherein, described ink also comprises tinting material, preferred pigments.
6. according to the printing-ink described in any one in claim 1 to 5, wherein, described ink also comprises solvent and optionally comprises additive.
7. overprint varnish zhe, it comprises nitration of lignin as at least one binder ingredients.
8. overprint varnish zhe according to claim 7, wherein, described nitration of lignin can be by being no more than at the temperature of 28 ℃ and solvent obtains with the alkaline xylogen of nitric acid nitrating under existing, and described solvent and water are immiscible and are inertia to nitric acid.
9. according to the overprint varnish zhe described in claim 7 or 8, wherein, described alkaline xylogen can obtain by making xylogen stand the processing of chemistry-thermomechanical, described chemistry-thermomechanical is processed under the additive existence being included in such as ethylene glycol, mechanical shearing under the top temperature of about 100-220 ℃ and under approximately 0.5 to approximately 10 atmospheric pressure, described additive reduces the softening temperature of described xylogen.
10. according to the overprint varnish zhe described in any one in claim 7 to 9, wherein, described ink comprises at least one extra tackiness agent, and described extra tackiness agent is selected from urethane resin, ketone resin or polyamide resin.
11. according to the overprint varnish zhe described in any one in claim 7 to 10, and wherein, described ink also comprises solvent and optionally comprises additive.
12. prepare printing-ink, particularly gravure printing ink or flexographic ink, or the method for overprint varnish zhe, and the method comprises the following steps:
-by nitrated alkaline xylogen, prepare nitration of lignin and described nitration of lignin is dissolved in acetone to obtain 50% acetone soln;
-acetone soln of nitration of lignin is mixed with one or more components that are selected from tinting material, at least one solvent and optional additive, described tinting material is preferably pigment.
13. methods according to claim 12, wherein, described nitration of lignin by alkaline xylogen is suspended in to nitric acid inertia, with the immiscible organic liquid such as tetracol phenixin of water in, and make this xylogen be no more than at the temperature of 28 ℃ with nitric acid reaction 2 to hour, most preferably 4 to 8 hours and preparation.
14. according to the method described in claim 12 or 13, wherein, after reaction finishes, water and use CCl
4wash described nitration of lignin.
15. nitration of lignin are printing-ink, particularly gravure printing ink or the flexographic ink described in any one in preparation claim 1 to 6, or the purposes in the overprint varnish zhe described in any one in claim 7 to 11.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN212/DEL/2012 | 2012-01-24 | ||
| IN212DE2012 | 2012-01-24 | ||
| PCT/EP2012/061821 WO2013110355A1 (en) | 2012-01-24 | 2012-06-20 | Printing ink or overprint varnish with renewable binder component |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104053732A true CN104053732A (en) | 2014-09-17 |
| CN104053732B CN104053732B (en) | 2016-09-28 |
Family
ID=46319147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201280067411.1A Expired - Fee Related CN104053732B (en) | 2012-01-24 | 2012-06-20 | There is printing-ink or the over print varnish of reproducible adhesive component |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9546287B2 (en) |
| EP (1) | EP2620480B1 (en) |
| CN (1) | CN104053732B (en) |
| BR (1) | BR112014018089A8 (en) |
| MX (1) | MX2014008899A (en) |
| PL (1) | PL2620480T3 (en) |
| RU (1) | RU2602866C2 (en) |
| WO (1) | WO2013110355A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2868720A1 (en) | 2013-11-01 | 2015-05-06 | Siegwerk Druckfarben AG & Co. KGaA | Printing ink with nitrated lignin ester as binder component |
| US20150126716A1 (en) * | 2013-11-01 | 2015-05-07 | Iowa State University Research Foundation, Inc. | Nitrated lignin ester and process of making the same |
| EP3124556B1 (en) * | 2015-07-31 | 2018-04-18 | Siegwerk Druckfarben AG & Co. KGaA | Water-based inks comprising lignin |
| EP3845391A1 (en) | 2016-08-11 | 2021-07-07 | HP Scitex Ltd. | Selective overcoat |
| US10189271B2 (en) | 2016-08-18 | 2019-01-29 | Eastman Kodak Company | Non-foaming aqueous particle-free inkjet ink compositions |
| US10138386B2 (en) | 2016-08-18 | 2018-11-27 | Eastman Kodak Company | Method of inkjet printing a colorless ink |
| EP3820913A1 (en) | 2018-07-12 | 2021-05-19 | Basf Se | Process for end functionalized acrylic oligomers via high temperature polymerization and efficient addition reactions |
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| US4957557A (en) | 1988-10-11 | 1990-09-18 | Westvaco Corporation | Submicron lignin dispersions |
| SU1643562A1 (en) * | 1988-10-12 | 1991-04-23 | Предприятие П/Я Р-6875 | Cellulose oligomer as binder for lacquers and method for its production |
| US4892587A (en) | 1988-10-24 | 1990-01-09 | Westvaco Corporation | Lignosulfonate additive-containing carbon black compositions |
| US5188665A (en) | 1992-01-24 | 1993-02-23 | Westvaco Corporation | Lignin amine salt-based binders for water-based black ink formulations |
| US5192361A (en) | 1992-01-27 | 1993-03-09 | Westvaco Corporation | Submicron lignin-based binders for water-based black ink formulations |
| DE10042900A1 (en) | 2000-08-31 | 2002-03-14 | Basf Ag | Aqueous colorant preparation for inkjet printing |
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| ATE287422T1 (en) | 2002-04-25 | 2005-02-15 | Sicpa Holding Sa | POLYURETHANE RESIN MADE OF HYDROPHILIC POLYOL COMPONENTS |
| DE60202442T2 (en) | 2002-04-25 | 2006-05-04 | Sicpa Holding S.A. | Polyurethane resin from hard ketone resins |
| DE60314112T2 (en) | 2003-07-04 | 2008-01-31 | Siegwerk Benelux Nv | Resin and ink for printing on shrinkable sleeves |
| ES2248687T3 (en) | 2003-07-11 | 2006-03-16 | Sicpa Holding S.A. | POLYURETHANE RESIN FOR COLOR INK. |
| EP1496072B1 (en) | 2003-07-11 | 2005-11-02 | Sicpa Holding S.A. | A polyurethane resin for white inks |
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2012
- 2012-06-20 WO PCT/EP2012/061821 patent/WO2013110355A1/en active Application Filing
- 2012-06-20 RU RU2014134536/05A patent/RU2602866C2/en not_active IP Right Cessation
- 2012-06-20 BR BR112014018089A patent/BR112014018089A8/en not_active IP Right Cessation
- 2012-06-20 PL PL12172738T patent/PL2620480T3/en unknown
- 2012-06-20 CN CN201280067411.1A patent/CN104053732B/en not_active Expired - Fee Related
- 2012-06-20 EP EP12172738.2A patent/EP2620480B1/en not_active Not-in-force
- 2012-06-20 US US14/374,153 patent/US9546287B2/en not_active Expired - Fee Related
- 2012-06-20 MX MX2014008899A patent/MX2014008899A/en not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2620480B1 (en) | 2014-04-16 |
| BR112014018089A8 (en) | 2017-07-11 |
| BR112014018089A2 (en) | 2017-06-20 |
| US9546287B2 (en) | 2017-01-17 |
| WO2013110355A1 (en) | 2013-08-01 |
| PL2620480T3 (en) | 2014-09-30 |
| EP2620480A1 (en) | 2013-07-31 |
| MX2014008899A (en) | 2014-11-14 |
| CN104053732B (en) | 2016-09-28 |
| US20150000559A1 (en) | 2015-01-01 |
| RU2602866C2 (en) | 2016-11-20 |
| RU2014134536A (en) | 2016-03-27 |
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